158837-63-9

Basic information

• Product Name: (1S,2S)-1-Phenyl-1-phthalimido-2-(dimethylamino)propane
• Synonyms: (1S,2S)-1-Phenyl-1-phthalimido-2-(dimethylamino)propane
• CAS NO: 158837-63-9
• Molecular Weight: 308.38
• Mol File: 158837-63-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1S,2S)-1-Phenyl-1-phthalimido-2-(dimethylamino)propane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-1-Phenyl-1-phthalimido-2-(dimethylamino)propane(158837-63-9)
• EPA Substance Registry System: (1S,2S)-1-Phenyl-1-phthalimido-2-(dimethylamino)propane(158837-63-9)

Safety Data

• Hazardous Substances Data: 158837-63-9(Hazardous Substances Data)

Upstream product

• 136918-14-4 phthalimide 
• 1201-56-5 (1S,2S)-N-Methylpseudoephedrine 
• 158837-61-7 O-<(1S,2S)-N-Methylephedrine>-N,N'-diisopropylisourea 

Downstream Products

• 919113-05-6 (1S,2S)-N,N-dimethyl-1-phenylpropane-1,2-diamine 

Relevant articles and documents

Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones

This article describes the synthesis of a library of structurally diverse bifunctional organocatalysts bearing both a quasi-Lewis acidic (thio)urea moiety and a Bronsted basic tertiary amine group. Sequential modification of the modular catalyst structure and subsequent screening of the compounds in the alcoholytic dynamic kinetic resolution (DKR) of azlactones revealed valuable structure-activity relationships. In particular, a "hit-structure" was identified which provides e.g. N-benzoyl-tert-leucine allyl ester in an excellent enantiomeric excess of 95%. The Royal Society of Chemistry 2006.

Application of the Mitsunobu reaction to ephedrines and some related amino alcohols. Aspects of intramolecular participation of the amino group

Inversion of configuration at the benzylic hydroxyl group of (1S,2S)-pseudoephedrine (2) to afford (1R,2S)-ephedrine is known to be a difficult process.The Mitsunobu reactions of 1 and 2 might offer a route to achieve such inversions.In fact Mitsunobu reactions on 1 and 2 are known to proceed via aziridines formed on intramolecular SN2 substitution by the amine functionality.The Mitsunobu reactions of N-methylated and N-benzylated ephedrines have been found to proceed via the corresponding aziridinium ions.These aziridinium ions can be opened (SN2 substitution) by nucleophiles like phthalimide and thiols.Intramolecular participation in 2 can be avoided by use of the tert-butyloxycarbonyl-(BOC) or benzyloxycarbonyl- (CBZ) protected derivatives.Mitsunobu reactions on these derivatives lead to inversion of configuration at the benzylic hydroxyl center.In contrast the BOC and CBZ derivatives of 1 are deprotected under Mitsunobu conditions.The Mitsunobu reactions of threo (1S,2S)-2-amino-1,3-propanediol have also been examined.An attempt to achieve protection by reaction with dimethylformamide dimethyl acetal led to the more substituted 2-oxazoline as established by X-ray crystallography.The desired inversion of configuration of the benzylic hydroxylic group was eventually achieved by protection of the amino substituent as the phthalimide and protection of the primary hydroxyl group as the tosylate.